Imidazol-1-YL-oxo-acetic acid tert-butyl ester → (2-benzo[1,3]dioxol-5-yl-acetylamino)-methyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester

HRID 1745417Notes

Reaction equation

HRID 1745417 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:16]2C[CH:14]([CH2:17][NH:18][C:19](=[O:30])[CH2:20][C:21]3[CH:29]=[CH:28][C:24]4[O:25][CH2:26][O:27][C:23]=4[CH:22]=3)[O:13][CH2:12][C:11]=2[S:10][C:9]=1N)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:32](OC(=O)C(N1C=CN=C1)=O)(C)(C)C>ClCCl>[C:1]([O:5][C:6]([C:8]1[C:16]2[CH:17]([NH:18][C:19](=[O:30])[CH2:20][C:21]3[CH:29]=[CH:28][C:24]4[O:25][CH2:26][O:27][C:23]=4[CH:22]=3)[CH2:14][O:13][CH2:12][C:11]=2[S:10][C:9]=1[CH3:32])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11217804Imidazol-1-YL-oxo-acetic acid tert-butyl esterHCID 695859102-amino-5-((2-benzo[1,3]dioxol-5-yl-acetylamino)-methyl]4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester

Product 1

HCID 131725675(2-benzo[1,3]dioxol-5-yl-acetylamino)-methyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the above crude 2-amino-5-((2-benzo[1,3]dioxol-5-yl-acetylamino)-methyl]4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (0.17 g, 0.38 mmol) in dichloromethane (5 ml) was added imidazol-1-yl-oxo-acetic acid tert-butyl ester (0.22 g, 1.14 mmol). The reaction mixture was stirred at room temperature for 18 hours, the volatiles evaporated in vacuo and the residue diluted with ethyl acetate. The organic layer was washed with hydrochloric acid (1% (v/v), 2×25 ml), saturated sodium bicarbonate (2×25 ml) and brine (2×25 ml). The organic layer was dried (MgSO4), filtered, concentrated in vacuo and the residue subjected to flash chromatography using a mixture of ethyl acetate/hexanes (1:2) as eluent, which afforded 0.12 g (55%) of 2-(tert-butoxyoxalyl-amino)-5-((2-benzo[1,3]dioxol-5-yl-acetylamino)-methyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester as an oil.

Workup

  1. customthe volatiles evaporated in vacuo
  2. additionthe residue diluted with ethyl acetate
  3. washThe organic layer was washed with hydrochloric acid (1% (v/v), 2×25 ml), saturated sodium bicarbonate (2×25 ml) and brine (2×25 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additiona mixture of ethyl acetate/hexanes (1:2) as eluent

Sources & evidence

ORD record
ord-fc11c135806746e5a15b18a5d85fe602
Source dataset
uspto-grants-2006_03
Patent number
US07019026B1

Reaction notes

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